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Scalable Synthesis of Orthogonally Protected β-Methyllanthionines by Indium(III)-Mediated Ring Opening of Aziridines

Author:
Li, Ziran, Gentry, Zachary, Murphy, Brennan, VanNieuwenhze, Michael S.
Source:
Organic letters 2019 v.21 no.7 pp. 2200-2203
ISSN:
1523-7052
Subject:
Gram-positive bacteria, Lewis bases, amino acids, aziridines, bacteriocins, chemical reactions, chemical structure, indium, peptide antibiotics, stereoselective synthesis
Abstract:
Lantibiotics are a class of peptide antibiotics with activity against most Gram-positive bacteria. Lanthionine (Lan) and β-MeLan are unusual thioether-bridged, non-proteinogenic amino acids, which are characteristic features of lantibiotics. In this paper, we report the facile stereoselective synthesis of β-methyllanthionines with orthogonal protection by nucleophilic ring opening of aziridines. This method leads to an expedient access to β-methyllanthionines and allows production of over 30 g of β-methyllanthionine in a single batch.
Agid:
6363038